Free download: The 8-Figure Exit Guide

The exit playbook for owners of $5M–$50M companies and businesses with $1M+ in EBITDA. Get your free copy →

“I think greed is healthy. You can be greedy and still feel good about yourself.”

That was, no joke, part of Ivan Boesky’s speech to the graduating business class at UC Berkeley in 1986.

I’m just finishing Den of Thieves for the first time, and that’s not only a hilarious thing to say during a commencement speech. It also had me drawing parallels between ’80s Wall Street greed and Silicon Valley’s AI boom today.

If you haven’t read this (very old) story, I’m about to spoil it for you (oh no):

A few months after that speech, Boesky’s massive insider trading scandal blew up, lol. Apparently, feeling good about yourself and staying out of prison are two different things.

The ’80s were a wild time in finance. The market was flying, and an innovation called junk bonds helped fuel a wave of takeovers. Suddenly, buyers could raise enormous sums of money to acquire companies that would have been out of reach before.

There was a lot of money to be made. And when money starts moving that quickly, some people get a little too comfortable cutting corners.

Boesky traded on inside information. Michael Milken, the junk bond pioneer, later pleaded guilty to securities-law violations. They were among the high-profile finance guys caught up in the greed rush (see what I did there). And those were only the ones who got caught.

But junk bonds didn’t force these guys to commit crimes. The boom in high-yield bonds created a lot of opportunity, and a lot of temptation.

Sound familiar?

I get a similar feeling watching AI right now. Money is flying into the space. Every company seems to have an AI strategy, even if that strategy is adding “AI” to its website and hoping nobody asks them to explain how an LLM actually works (silly question, because nobody knows).

It’s easy to get sucked into the hype. Especially when it looks like everyone else is getting rich the best way: quickly.

Now, innovation isn’t the root of all evil. Wall Street is.

Kidding, sort of.

But seriously, this financial renaissance also produced some of the biggest pioneers still driving markets today. KKR grew rapidly during the ’80s through LBOs. Stephen Schwarzman co-founded Blackstone in 1985, using a similar model. Turns out not everyone needed a prison sentence to make a name on Wall Street.

With AI, the shortcuts probably won’t land you in prison. But, like Boesky and Milken, cutting corners can do serious damage to your reputation.

Examples: a website full of AI-slop copy. I’ve literally come across clients with fake customers + testimonials (clearly from AI) on their LIVE site.

Or the client who sends you an email that starts with, “I got that all polished for you, simply copy & paste this into your email…” without realizing they included the AI instructions.

Each shortcut saves a little time or makes a little money. But together, they can chip away at the trust and personality you spent years building.

Turns out your customers notice when you replace your company’s voice with a robot that writes sentences like, “It’s not just electrical work, it’s the pulse of a home.” Yuck.

Instead of killing your reputation, use AI to build a stronger company. Help your team respond to customers faster. Take repetitive admin off their plates. Make your hard-earned knowledge easier for the next employee to find. All this stuff can make your company easier to run, which can also make it easier to sell (and more valuable).

If you don’t know where to start, pay a niece or nephew to help automate a low-risk task you hate (like consolidating your monthly receipts into a spreadsheet) with an AI agent.

AI is so easy to use that it lets us fall into one of our greatest weaknesses: laziness. Don’t become a lazy user of AI or you might just end up in AI jail.

Thinking about selling your business? A confidential, no-pressure conversation can help you identify what makes your company valuable and where to strengthen it. Schedule a call →

Speak naturally. Send without fixing.

Wispr Flow turns your voice into clean, professional text you can send the moment you stop talking. No rough transcription you have to clean up. Actual polished text, ready for email, Slack, or any app.

Speak the way you think. Go on tangents. Change your mind mid-sentence. Flow strips the filler, fixes the grammar, and gives you text that reads like you spent five minutes writing it.

Start flowing free

founder fitness

WOD: “Take a wide stance”

3 rounds:

• 12 wide-stance goblet squats

• 10 dumbbell Romanian deadlifts

• 8 reverse lunges per leg

• 45 seconds on the bike or rower

Rest 90 seconds between rounds. Use a comfortable stance and controlled weight. Swap the goblet squats for bodyweight squats if needed.

founder challenge: the AI automation challenge

Write down five repetitive tasks in your business that AI could help automate. Think meeting summaries, first drafts, sorting enquiries, scheduling follow-ups or documenting a process.

Pick one. Test it this week with non-sensitive information and check the result yourself. Done means you have a list of five and one tested workflow you can improve or discard.

Don’t know how to use AI? Pay a high school kid to show you. Or ask your nephew. He’s probably already using it to avoid doing his homework.

Want a full week of these? Try the free 7-day founder fitness challenge →

deal breakdown

This week: a Miami plumbing company with $1M+ in EBITDA.

see how your business would score → take the free Exit Audit

my plugs

• Schedule a confidential call to discuss selling your business.

• Book your free Exit Audit: We guarantee we’ll find hidden profit in your business. Start here →

• Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater’s deal portal HERE

• Download a free copy of The Lower Middle Market Exit Guide

• Subscribe to my YouTube Channel

• Follow me on Instagram and LinkedIn

every second counts

The exit playbook for owners of $5M–$50M companies and businesses with $1M+ in EBITDA. Get your free copy →

“You suck.”

Apparently, that’s what Jensen Huang (Nvidia’s co-founder) tells himself in the mirror. Yes, really lol.

After a great quarter, an Nvidia executive recalled Huang saying:

“I look in the mirror every morning and say: ‘You suck.’”

Most people start with coffee and a little existential dread (no, just me?). Jensen skips straight to the performance review.

As of October, Jensen’s net worth was around $200 billion. We all know money doesn’t buy happiness. But apparently, it doesn’t buy a quieter inner critic either.

I meet a lot of entrepreneurs with that same mentality. Sometimes it comes from how they were raised, a rough time at school, or a chip they’ve carried for years. Sometimes it’s simply the urge to prove themselves wrong.

Jensen has said, “In order to do something incredible, you have to suffer.” Asked on the Acquired podcast whether he’d do the founder journey again, knowing what he knows now, he said, “I wouldn’t do it.” He described building Nvidia as “a million times harder” than he expected.

A quick recap of the road there:

• Nvidia’s first chip flopped: The NV1 failed in the marketplace. Back to the drawing board.

• Running out of money: Nvidia had about six months of cash left while building the RIVA 128. Nothing like a potential bankruptcy to spice up a product launch.

• He kept making long-term bets: Turns out, CUDA (I won’t pretend I know what that is) is really useful, long before today’s AI demand was obvious.

• The bets compounded: Years of testing, learning and improving helped turn a struggling chip company into a business at the centre of the AI boom.

Not exactly a straight line from good idea to billionaire.

Jensen’s morning routine sounds brutal, but there’s an important distinction: suffering for its own sake is different from accepting the hard parts of building something you care about.

No big personal achievement comes for free.

I wrote in June that Stoicism isn’t about chasing pain. It’s about choosing the right pain, the kind that builds competence, without turning self-punishment into a personality. Learn to suffer joyfully →

The goal isn’t to become better at suffering. It’s to learn to love the journey, keep getting better, and celebrate a win before immediately inventing a new problem.

Thinking about selling your business? A confidential, no-pressure conversation can help you understand what a buyer might value and what you may want to strengthen before a process. Schedule a call →

Leave Granola and get up to 12 months free of Wispr Flow Notetaker + Dictation

If you have paid time left on an individual Granola plan, we'll match it with a Wispr Flow subscription that includes Notetaker and dictation, and add bonus time, up to 12 months total. Sign in or create a Wispr account and submit proof of your plan to check eligibility.

Try Notetaker Free

founder fitness

WOD “Denny’s detour” (12-minute AMRAP):

• 10 dumbbell deadlifts

• 8 push-ups

• 10 goblet squats

• 30 seconds on the bike or 150-metre row

Founder challenge: make 10 hard calls

Ari Emanuel built his career as a talent agent by “rolling the calls,” sometimes making 100-plus calls a day. He says the 10,000-hour rule doesn’t hold a candle to making 10,000 hard calls.

As he puts it, “The ten-thousand-phone-call rule is undefeated.”

But today is your lucky day: you only have to make 10.

• Call a prospect or an old lead.

• Ask your boss for a promotion or a past client for a referral.

• Give a co-worker the honest feedback you’ve been avoiding.

Want a full week of these? Try the free 7-day founder fitness challenge →

deal breakdown

This week’s deal breakdown is of the ‘highest volume’ med spa on the west coast with VERY (🙄) high margins… leaving a few question marks

see how your business would score → take the free Exit Audit

my plugs

• Schedule a confidential call to discuss selling your business.

• Book your free Exit Audit: We guarantee we’ll find hidden profit in your business. Start here →

• Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater’s deal portal HERE

• Download a free copy of The Lower Middle Market Exit Guide

• Subscribe to my YouTube Channel

• Follow me on Instagram and LinkedIn

every second counts

Free download: The 8-Figure Exit Guide

The exit playbook for owners of $5M–$50M companies and businesses with $1M+ in EBITDA. Get your free copy →

In 2011, XPO Logistics had $175 million in revenue.

Six years later, it had $15 billion.

That’s about 86 times the size. And no, Brad Jacobs (hilariously, the author of a book titled “How to Make a Few Billion Dollars”) did NOT do this with organic social media posts.

No, he made a series of strategic acquisitions that put the company into a new stratosphere of growth.

His plan had three parts:

1. Buy the right pieces: XPO targeted non-asset-based logistics companies, especially truck brokers with $30 million to $200 million in revenue. The idea was to buy at a lower multiple than the combined company would trade for (finance bros call this “multiple arbitrage”).

2. Build where it made sense: Jacobs didn’t throw the baby out with the bathwater. He still planned to open 20 new locations from scratch. No acquisition required.

3. Make the whole machine better: Invest in technology, shared services, and operating discipline so new and acquired teams could work at a larger scale.

Over the next six years, XPO made 13 acquisitions. That might sound like a lot, but it wasn’t a spray-and-pray approach. It was about patiently finding the right acquisitions to grow the business.

This makes a strong case for buying instead of building, which is a decision buyers often grapple with. I find inexperienced buyers often frame it the wrong way:

“Why should we buy this business when we can build it ourselves?”

Sometimes they’re right. If you can hire a good salesperson, open a new location, and win customers for less than the cost and risk of buying, build it.

But don’t forget the invisible price tag: time.

A new location can take years to earn trust. Building a marketing engine that produces predictable leads can cost millions in start-up capital. Even harder, a great team can take years to recruit, train, and keep.

Acquisitions can act like the world’s least exciting time machine. You get the people, customer relationships, and know-how on day one. But then the real work begins: keeping the team, integrating systems, and making sure the change doesn’t break the reason customers chose the business in the first place.

So don’t ask only, “What’s the purchase price?” Ask, “What would it cost us to build this, how long would it take, and what could go wrong after we own it?”

This same question comes up in the lower middle market. Do you build a marketing engine and hire talent from scratch, or buy a business with repeat customers, proven lead flow, and a team already in place? Buying can save years, but costs more and key people may leave. Building can be cheaper, but takes time. First identify the gap, then compare the cost, timeline, and risk of each path.

If you’re the owner thinking about a sale, don’t stop at “we make $1 million of EBITDA.” Show the buyer what would take years to recreate: repeatable leads, a team that knows how to deliver, and customer relationships that keep coming back.

The best answer is often both. Buy the capability that would take years to recreate. Build where you have scarce expertise and resources.

Thinking about selling your business? A confidential, no-pressure conversation can help you understand what a buyer might value and what you may want to strengthen before a process. Schedule a call →

Unify Your Teams and Tech Stack With HubSpot

Connect your customer data, teams, and tools without the hassle of complex integrations or lengthy setups. One easy platform gives marketing, sales, and service teams a unified customer view and the tools to turn it into growth.

Why HubSpot and what's new
• Generate leads and automate marketing with Marketing Hub
• Build your pipeline and close more deals with Sales Hub
• Scale customer support and drive retention with Service Hub
• Keep customer data clean, connected, and actionable with one, unified platform

Join 306,000+ in over 135 countries using HubSpot to grow their businesses.

See what a more connected approach to growth can do for you and your team. Get setup quickly and start checking off your hardest tasks.

Get started free

founder fitness

WOD “Push Power” (10-min EMOM, at the bench):

• Odd minutes: 10 DB bench press (50-60s)

• Even minutes: 12 push-ups + 8 DB push press (35-40s)

founder challenge: buy or build your biggest gap

Pick the biggest constraint in your business: repeatable customer leads, a marketing engine, or talent. Choose one real example and answer:

1. What would it cost and how long would it take to build?

2. What would buying give us on day one?

3. What could disappear after the deal closes?

For example, if referrals drive most of your new customers, could you build a reliable marketing channel, or would buying an established lead engine save years? If you need a senior operator, can you recruit and train one, or does an existing team bring customer relationships and know-how that are hard to replace?

Write down the path you’d choose and the first step you’ll take this week.

deal breakdown

This week’s deal breakdown: a $3M digital agency with nearly $1M in SDE—and the buyer questions behind the headline numbers.

see how your business would score → take the free Exit Audit

my plugs

• Schedule a confidential call to discuss selling your business.

• Book your free Exit Audit: We guarantee we’ll find hidden profit in your business. Start here →

• Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater’s deal portal HERE

• Download a free copy of The Lower Middle Market Exit Guide

• Subscribe to my YouTube Channel

• Follow me on Instagram and LinkedIn

every second counts

[NEW] Free download: The 8-Figure Exit Guide

The exit playbook for owners of $5M–$50M companies and businesses with $1M+ in EBITDA. Get your free copy →

Ari Emanuel (the real-life version of Ari Gold from Entourage) says he and his team spent four months negotiating UFC rights with ESPN.

The deal was huge: ESPN was reportedly paying about $300 million a year to show UFC fights. Dana White still wanted more.

Ari called Dana with the offer: eight UFC shows on ESPN, with the rest on ESPN+. His team was “sweating bullets,” he says. Dana's response: “I'm not doing that unless we have 10.”

Ari's reply: “We have nobody else right now.” Not exactly the line you want to hear in a negotiation.

Side note: I, unfortunately, empathize. We have our fair share of irrational client demands show up right before closing too. 🙄

Emanuel went back to ESPN and, in his words, “went crazy,” literally screaming on the phone that they needed 10 instead of 8.

While the delivery was, questionable, Ari had a point: more events would help create stars, give fans a reason to pay for ESPN+, and help new viewers understand the sport. ESPN conceded, and Dana got his two extra shows.

The UFC and ESPN are worlds away from a $10 million HVAC company. But the same lesson applies: the person with the most leverage may not be at the negotiation table.

In a smaller deal, it might be the buyer or seller. More often, it’s the “advisor” who’s really just a golf buddy, or an accountant or lawyer too busy to get the deal closed (yes, we’ve actually heard this excuse for killing a deal before).

As M&A advisors, we’re the intermediaries. Some days it feels like being a kid while your parents fight. Except instead of hiding in our room, we have to jump into the middle and try to get them talking again. Ari’s tactic was a full regression to childhood: throw a tantrum to distract the parents and force them to make-up 😂

Lesson: before you celebrate the number, find out who else needs to say yes.

Thinking about selling your business? We can help you spot the people, terms and surprises that could derail a deal before they show up in diligence. Start with our free and NEW Exit Audit —> here

Some teams never seem to stop moving. They're on Attio, the agentic CRM.

Every customer signal is captured in one shared context layer, always current and compounding. Agents and workflows build pipeline, chase every buying signal, and move deals forward, an always-on revenue engine running alongside your team.

With Attio, you’ll get:

• Leads automatically prioritised and routed to the right rep

• Expansion and risk signals caught the moment they land

• Follow-ups written in your voice, already there when you arrive

Teams like Parallel, Turbopuffer, and Wordsmith build on Attio. Are you one of them?

Get started now

founder fitness

fitness challenge: WOD “Leg Engine”

Did this workout on Tuesday and my legs are crushed 😅

8-minute AMRAP, one pair of DBs at the rack:

• 10 goblet squats

• 10 DB Romanian deadlifts

• 12 reverse lunges (6 per leg)

Use 50s as a starting point: one DB for the goblet squat, the pair for RDLs and lunges.

founder challenge: audit one price

Pick one service or product. Review three recent quotes or invoices, compare the price with the time and cost to deliver, then decide whether to keep it, raise it or change the scope. Done means the decision is written down and either applied or scheduled for this week.

want a full week of these? try the free 7-day founder fitness challenge →

deal breakdown

This is an incredible clip from David Senra’s founders podcast:

😂 😂 😂 This interview is UNREAL. Ari Emanuel was on David Senra’s Founders podcast and he talked about negotiating the UFC deal with Lorenzo and Frank Fertitta. Ari’s approach to getting a… | Morgan Tate

😂 😂 😂 This interview is UNREAL. Ari Emanuel was on David Senra’s Founders podcast and he talked about negotiating the UFC deal with Lorenzo and Frank Fertitta. Ari’s approach to getting a number on the table was… unique: “Close your eyes… What would make you happy? What’s the number that you see when your eyes are closed?” The response: “It’s a big f****** number, Ari.” “And it starts with a four, right?” What a way to ask someone their price 😂 Ari went straight to the human side of the negotiation. In a lot of SMB deals, that’s where the real conversation starts: what number would actually make you happy? First-time buyers often miss this. They get stuck arguing over what a business is worth instead of understanding what the seller actually wants. And honestly (I probably shouldn’t post this as a M&A advisor) but a lot of valuations are made up. Purchase price, at the end of the day, comes down to how much a buyer is willing to pay and what a seller is willing to take. That’s it. So, stop telling a seller about your discounted cash flow analysis 🤓 and have them close their eyes and picture their number, like Ari LOL. I’m doing a full breakdown of Ari’s ESPN deal tomorrow in my newsletter Subscribe through the link in my LinkedIn bio.

LinkedIn

my plugs

• Schedule a confidential call to discuss selling your business.

• Book your free Exit Audit: We guarantee we'll find hidden profit in your business. Start here →

• Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater's new deal portal HERE

• Download a FREE copy of The Lower Middle Market Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

my plugs

• Schedule a 15-minute consultation call to discuss buying or selling your business.

• Subscribe to my newsletter for weekly insights on business and founder fitness.

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials - X + insta + linkedin

every second counts

The exit playbook for owners of $5M–$50M companies and businesses with $1M+ in EBITDA. Get your free copy →

Right before the Mayans predicted the end of the world, Mark Zuckerberg agreed to pay $1 billion for Instagram. Surely a sign the good times were behind us.

The company was two years old. It had about 30 million users and no revenue.

We’re all the idiots now, but at the time, a billion dollars for an app that put a sepia filter on your latte seemed like a pretty bad deal.

But, like the Mayans, we got that one wrong.

Most of the time, a billion dollars is too much to pay for photos of brunch. But Zuck (we’re close like that) wasn’t paying for filters.

He was buying the next place people would spend their attention. Zuck saw it before almost everyone else did.

While Facebook was the product he invented. His greatest talent, time and time again, has been understanding trends and what to acquire next.

Instagram for $1 billion. WhatsApp for roughly $19 billion. Oculus for $2 billion. People are still laughing at that last one, but it could end up being the biggest deal of them all. He did not need every important idea to originate inside Facebook. He needed the right ideas to end up inside the company.

That distinction made him one of the best serial acquirers in tech.

And yes, the Instagram deal looks like a steal now.

By 2018, Bloomberg Intelligence estimated that Instagram would be worth more than $100 billion as a standalone company—a 100x increase over the announced purchase price in six years.

Then court filings gave us a hard number: Instagram generated $32.4 billion of advertising revenue in 2021 alone. That was more than 32 times the headline acquisition price in a single year.

While we don't know the exact amount of profit Instagram has generated during that time, it doesn't take an Einstein to realize that this was a home run.

The inexperienced buyer asks, “How did they arrive at this valuation?” The seasoned dealmaker asks, “What is this business worth in my hands?”

Valuation is part art, part science. But first-time buyers often approach it like a math problem with one correct answer. At the end of the day, the purchase price is simply what one specific buyer is willing to pay.

A business can look expensive to a financial buyer and cheap to a strategic one. One sees the existing cash flow. The other sees customers, distribution or a capability that would take years to build.

Instagram had one set of financials, but it did not have one value. To everyone else, it was an app with no revenue. To Facebook, it was the future of mobile attention.

A great acquisition is not cheap on the day you buy it. It becomes cheap because of what you do with it afterward.

Important note: price still matters. Overpaying for a mediocre business remains a reliable way to ruin your week or life (kidding). You need to understand the cash flow, the risks, and your competitive advantage. What can you see that another buyer cannot? What would take you five years to build but could be acquired tomorrow?

Sometimes the smartest way to invent the future is to buy it before everyone agrees on what it is worth.

Thinking about buying a business? Create your free Buyer Profile and get access to opportunities that fit what you are actually looking for. Create your profile →

founder fitness

fitness challenge

20-minute AMRAP:

1. 10 kettlebell swings

2. 8 push-ups

3. 10 goblet squats

4. 200-metre row or 45 seconds on the bike

founder challenge: make a build-or-buy list

Write down the three capabilities your company will need most over the next two years. For each one, ask: should we build it, partner for it, or buy it?

Most founders default to building because it feels cheaper. It usually isn’t once you account for your time, the learning curve, and the cost of waiting.

Want a full week of these? Try the free 7-day founder fitness challenge →

deal breakdown

What is a civil contractor with $2 million in EBITDA actually worth? Here are the factors that determine the multiple.

resources of the week

• Check out this great profile of Mark Zuckerberg

• Don’t buy a bad business - here’s my 8 questions you should ask

• Is your business ready to sell? read this founder’s guide

my plugs

• Schedule a confidential call to discuss selling your business.

• Book your free Exit Audit: We guarantee we'll find hidden profit in your business. Start here →

• Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater's deal portal HERE

• Download a free copy of The Lower Middle Market Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + Instagram + LinkedIn

every second counts

The exit playbook for owners of $5M-$50M companies and businesses with $1M+ in EBITDA. Get your free copy →

In 1994, Quaker Oats paid $1.7 billion for Snapple. Three years later, Quaker sold Snapple for $300 million.

Quaker really put the “Oh snap!” in Snapple. My apologies, hand over the heart that wasn’t written by AI. Which probably makes it worse.

Anyways.

Quaker lost 82% of the value in three years (honestly impressive). But this is not only a cautionary tale about selling your business to the highest bidder. It is also a masterclass in how to fail at acquiring one.

The story: Snapple was started by three childhood friends from Brooklyn selling juice to health food stores out of the back of a truck (pretty sure this is a coming of age ritual in Brooklyn).

As the brand grew, it stood out because the marketing was super weird: Wendy the Snapple Lady answering fan mail on TV, plus sponsorships with radio hosts the big brands would not touch. Customers did not just buy Snapple. They were in on the joke.

In 1992, private equity firm Thomas H. Lee bought the company for about $135 million. Two years later, riding the iced tea boom, they sold it to Quaker for $1.7 billion. As a sell-side outcome, it is one of the great flips of all time.

The mechanics of the disaster: Quaker owned Gatorade and assumed the same playbook would work: pull the product into warehouses and push it through supermarkets. But Snapple did not run on supermarkets. It ran on a scrappy network of independent distributors who put single bottles in delis, gas stations, and corner stores.

Quaker tried to force the distributors to hand over their best accounts. The distributors revolted. Then Quaker killed the weird marketing that made the brand feel human. Sales fell off a cliff, and Quaker eventually paid a price so low it barely covered the marketing budget they had burned. The kicker: the next owner, Triarc, brought back the quirk, rebuilt distributor relationships, and sold Snapple three years later for roughly $1.45 billion.

What the sellers did right: Thomas H. Lee sold at the top, to a strategic buyer, in cash. When a buyer with a big strategy pays a big premium, the seller's job is to say yes and close fast.

What went wrong, and why it matters if you are thinking of buying a business: Quaker bought the brand but did not understand why it worked. Snapple's real asset was not the logo. It was the distributor relationships and the oddball culture.

We hear all the time that buyers have a bunch of new ideas they want to bring into a business. Honestly, it always makes us nervous.

Your job after closing is not to prove how smart you are. It is to understand the machine before you start pulling levers.

How to fail at acquiring a business:

1. Assume your old playbook will work: What worked in your last company may be completely wrong for the one you just bought.

2. Standardize the things that made the business special: The weird marketing, unusual culture or scrappy sales process might look inefficient. It might also be the reason customers care.

3. Alienate the people who actually hold the relationships: Employees, distributors, suppliers and referral partners can carry more value than anything on the balance sheet.

4. Chase synergies before you stabilize the business: Cost savings look great in a spreadsheet but can kill your relationship with customers.

5. Change too much, too quickly: Sometimes the smartest thing a new owner can do is pump the brakes, leave the business alone, and spend the first year learning why it works.

The best buyers earn the right to make changes.

They listen first. They protect the people and relationships that drive the business. Then they introduce tweaks and optimizations slowly, with evidence that the changes will actually help.

The takeaway in one sentence: before you improve the business you bought, make sure you understand what you cannot afford to break.

Thinking about buying a business? Create your free Buyer Profile and get access to opportunities that fit what you are actually looking for. Create your profile →

founder fitness

fitness challenge

At the gym, 5 rounds:

1. Front squat: 5 reps (moderate)

2. Incline dumbbell press: 8 reps

3. Kettlebell swings: 15 reps

4. Bike or row: 40 seconds hard

Rest 90 seconds between rounds.

founder challenge: build one SOP

Pick the task that lives entirely in your head (or a key employee's head), film a 5-minute video (I like Loom or Supercut.ai) walking through it, and let the AI draft the step-by-step SOP for you. Once you figure that out, do that every day for a month and you'll have fully documented SOPs for your business. We save all of our SOPs within Notion but you can use a tool like Google Docs to make it really easy for your employees to find them.

want a full week of these? try the free 7-day founder fitness challenge →

deal breakdown

“Is this 3x EBITDA restoration business a good deal? Or is something up?”

see how your business would score → take the free Exit Audit

my plugs

• Schedule a confidential call to discuss selling your business.

• Book your free Exit Audit: We guarantee we'll find hidden profit in your business. Start here →

• Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater's new deal portal HERE

• Download a FREE copy of The Lower Middle Market Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

The exit playbook for owners of $2M-$50M companies and businesses with $1M+ in EBITDA. Get your free copy →

In 2007, Blackstone (conspiracy theorists going crazy rn) took Hilton private for approximately US$26 billion.

A year later, the financial system melted down. Credit froze, commercial real estate got crushed, and travel slowed.

Perhaps the worst time in human history to complete a massive leveraged buyout of hotels.

Sweating like a crypto bro at tax time, Blackstone had a debt problem.

By 2009, Hilton's annual revenue had fallen about 15%, from roughly US$8.9 billion to US$7.6 billion. While their revenue disappeared, the debt did not (spoiler: this doesn’t work with the credit card companies either).

On the surface, this may not feel tangible to a small business owner. After all, the Hilton is an iconic global brand with thousands of hotels and billions of dollars.

But if you backspace a few of the zeroes - this can happen on any Mainstreet deal.

Take a $10 million business with a skinny 10% EBITDA margin. It produces $1 million of EBITDA after paying the owner a market salary.

Now subtract $700,000 of annual debt service and another $150,000 for taxes, equipment and working capital. The owner can distribute roughly $150,000. Debt service coverage is 1.43x. Profitable, but tight.

Now cut revenue in half to $5 million.

Even if the 10% margin somehow survives, EBITDA falls to $500,000. The $700,000 debt payment does not move. Before replacing a truck or paying taxes, the company is already $200,000 underwater. Ouch.

And that is the optimistic version. Most costs do not fall neatly with revenue, so skinny margins usually get skinnier.

The company did not become slightly less profitable. It went from paying the owner a $150,000 distribution to needing someone to inject $350,000 just to get through the year.

Zoom out far enough and the aristocracy and us plebiscites share the same problem:

Forces outside our control can flip our businesses upside down.

This also happens in lower-middle-market deals:

• Interest rates rise after the LOI is signed.

• A customer representing 20% of revenue leaves during diligence.

• Inflation compresses margins before the buyer's quality of earnings is finished.

• A key employee quits without notice.

• The government changes a policy that the business model depends on.

Some unfortunate news: bad stuff will continue to sucker punch us for the rest of our lives. But it’s not all bad.

The silver lining is that difficult periods force action. Strong businesses are often built when standing still is no longer an option.

So here is what Blackstone did.

Hilton cut costs, kept expanding internationally and moved further toward an asset-light model. Blackstone, doing what it does best, brutally negotiated with lenders.

By 2010, the restructuring had reduced Hilton's debt by nearly US$4 billion and extended major maturities to 2015.

That bought life's most scarce resource: time.

And time changed the outcome.

Hilton returned to the public market in 2013. The IPO raised approximately US$2.35 billion, but Blackstone did not cash out. It still owned roughly 76% of the company after the offering.

It sold down that position over the next five years.

In 2018, Blackstone sold its final 15.8 million Hilton shares for about US$1.3 billion. By then, the investment had reportedly generated approximately US$14 billion in profit.

See? There was a happy ending: the billionaires became richer.

Okay, okay, if that doesn’t warm your heart, here’s what it means if you want to sell your business:

1. Keep running the company: Miss a $500,000 EBITDA forecast by 10% and you lose $50,000 of earnings. At a 6x multiple, that can become a $300,000 price cut.

2. Know your runway: Maintain a 13-week cash forecast and track working capital, covenants and debt maturities.

3. Keep more than one path alive: One buyer or one lender is a single point of failure. Competition protects both price and certainty.

4. Share bad news early: Buyers can solve known problems. Surprises discovered in diligence become re-trades.

5. Fix the structure when the business is still good: A strong company can still have the wrong debt, timing or deal terms. Change them before the clock runs out.

You cannot control the next rate decision or customer departure. You can control your cash, reporting, contracts, management team and options.

Build a business that can absorb the shock without losing the deal.

Thinking about selling your business? We can help you identify the issues most likely to derail a deal before a buyer finds them. Schedule a confidential call →

founder fitness

fitness challenge:

At the gym, 4 rounds:

1. Trap-bar deadlift: 6 reps (or 10 dumbbell Romanian deadlifts)

2. Incline dumbbell bench press: 10 reps

3. Chest-supported row: 12 reps

4. Reverse lunges: 8 reps per side

5. Bike or row erg: 45 seconds hard

Rest 2 minutes between rounds. Choose weights that leave one or two good reps in the tank.

founder challenge: talk to five customers

Book five 20-minute conversations with current or former customers this week. Do not pitch them anything. Ask:

1. What problem were you trying to solve when you hired us?

2. What nearly stopped you from choosing us?

3. What part of working with us has been most valuable?

4. What is one thing we could make easier?

Write down their exact words and look for the answer that appears more than once. Turn that pattern into one concrete improvement to your offer, process or messaging before next Friday.

want a full week of these? try the free 7-day founder fitness challenge →

deal breakdown

Check out my last deal teardown

see how your business would score → take the free Exit Audit

P.S. I just hosted buyer office hours, answering some of the hottest questions I get from business buyers. You can watch a recap of that here.

my plugs

• Schedule a confidential call to discuss selling your business.

• Book your free Exit Audit: We guarantee we'll find hidden profit in your business. Start here →

• Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater's new deal portal HERE

• Download a FREE copy of The Lower Middle Market Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

The exit playbook for owners of $2M-$50M companies and businesses with $1M+ in EBITDA. Get your free copy →

In October 1988, the CEO of RJR Nabisco tried to buy his own company for $75 a share.

Six weeks later, it sold for $109 a share. He was not the winning buyer.

That six-week saga became Barbarians at the Gate, the most famous deal book ever written.

On the surface, it has nothing to do with a Main Street deal. Private jets, egregious corporate spending, and a $25 billion price tag.

But strip away the spectacle, and there is a core lesson that applies to every M&A deal: competitive tension changes the selling price.

The story: Ross Johnson was a salesman who charmed his way to the top of one of America's biggest (and most random) consumer companies: Oreos, Ritz crackers, and… cigarettes. He ran it like a personal kingdom with pro golfers on the company payroll and bougie Manhattan apartments for executives.

RJR’s stock price was stuck, so Johnson decided to take the company private with a management buy-out. He offered $75 a share, a $17 billion valuation. He assumed the board would wave it through since he was buddies with them all. And, at least in the market’s opinion, the business wasn’t worth all that much anyway.

Narrator voice: “Ross Johnson was incorrect.”

What happened: The board (by law) was required to form a special committee and run an auction process.

KKR (one of the most famous private equity firms) could smell the blood in the water. The other sharks (private equity groups) also started to circle. The bids climbed to Ross’ horror: $90, $100, $106.

KKR eventually won at $109 a share, roughly $25 billion. The final price was 45% higher than the opening offer.

Keep in mind, this is the exact same business (this was only a six-week process). The only thing that changed was buyer competition.

What this means if you’re planning to exit your business:

1. One buyer is not a market: An unsolicited offer from a competitor, employee, or “guy you know” is probably not the best bid because nothing is pushing their number higher.

2. Do not lock in with a single buyer. Run a process: The board made every buyer aware they could lose. That fear is worth more than almost any negotiating tactic.

3. Judge the deal structure, not the asking price: If your price includes an earn-out or seller financing, you need to understand how much cash (after tax) you will actually get out of the deal. The answer may surprise you.

The first offer tells you someone wants your business. Their second offer tells you what they think it’s worth.

Thinking about selling your business? A confidential, no-pressure conversation about what yours is worth and what a sale would actually look like. Schedule a call →

deal breakdown

This two-year-old pest control brand is asking $11 million on $2.65 million of EBITDA. The 4.1x multiple looks cheap, but with one SKU driving 85% of sales. My biggest question: why sell now?

see how your business would score → take the free Exit Audit

founder fitness

fitness challenge: the foundational five

At the gym, 5 rounds:

1. Back squat: 5 reps (moderate-heavy)

2. Strict press: 8 reps

3. Barbell rows: 10 reps

4. Row erg: 45 seconds hard

Rest 2 minutes between rounds.

founder challenge: energy drainers vs. energy gainers

Draw a T chart on a piece of paper. Left column: the work tasks that drain your energy. Right column: the ones that give you energy. Then eliminate one drainer this week by delegating it, hiring for it, or cutting it entirely.

A business built around your energy gainers is easier to grow—and a lot easier to step away from.

want a full week of these? try the free 7-day founder fitness challenge →

my plugs

• Schedule a confidential call to discuss selling your business.

• Book your free Exit Audit: We guarantee we'll find hidden profit in your business. Start here →

• Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater's new deal portal HERE

• Download a FREE copy of The Lower Middle Market Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

Thinking about selling your business?

A confidential, no-pressure conversation about what your business is worth and what a sale would actually look like. Schedule a call →

The greatest attribute of an entrepreneur is often their achilles heel.

Mine was decisiveness. In startup circles, “analysis paralysis” is the insult reserved for people who think too much and act too little.

I avoided overthinking like the plague, yet found myself a victim of a different disease = being a lazy thinker.

The big problem with under-thinking strategic decisions isn’t the short-term impact. It’s that the cost of a wrong decision compounds and shows up 6–12 months later, when it’s almost impossible to reverse course.

That’s exactly how my last start-up, DealBuilder, ended up with five products with almost zero revenue. We would have a “great” idea, often accompanied by a “How hard could it be?” question. After a few minutes of deliberations we’d go, “I don’t really see the downside” and get to work. This process makes me cringe when I think back on it.

Our delusional optimism came from failing to use a simple framework - best put by Jeff Bezos: one-way door and two-way door decisions.

A two-way door decision is easily reversible. For example: changing your company logo. If your customers hate the logo, it’s pretty easy to revert back to the original (take note: Jaguar).

A one-way door decision is hard or impossible to reverse. Lowering your pricing (good luck raising it back) or the big ones: taking on a business partner, signing a long-term lease, or selling your company.

Bezos says to walk through two-way doors with speed and comfort, and to treat one-way doors slowly, deliberately, and carefully.

Our mistake at DealBuilder was treating every door as a two-way door.

This is a mistake I have been desperate to avoid with Breakwater. We have been deliberate in slowing our growth - to ensure sustainability of our core operating model. At each pivot turn over the last year, we’ve tested whether the decision we are making is a 1-way or 2-way door.

So how do you test this? We’ve found the best filter is a one-sentence test.

Explain the idea to a colleague and let them ask one question: “What’s the end goal?” If you stammer out a long-winded answer with four different objectives, you’re off track. If you can answer in one confident sentence, you might be onto something:

• “This campaign gets us 8 signed sell-side clients, worth $X in fees when those deals close.”

• “This hire frees up 15 hours of my week to close deals, which is worth $Y a month.”

• “This system lets us run 5x the deal volume without adding headcount.”

In contrast, when I ask many business owners, “What would be the purpose of that decision?” many do not have a concrete answer. I’m guilty of this more than anyone.

This is what I’ve spent the past year doing at Breakwater. Deep, slow, deliberate thinking on the one-way doors. My younger self would have laughed at it as overthinking… which is also why my younger self was broke 😅

You should answer every big decision in your business within a single sentence. If you can’t, your thinking is half-baked, which is the fastest way to go broke.

new videos on youtube

I am back to (try) and post more regularly on YouTube focused on buying & selling businesses. If that’s of interest, make sure to subscribe:

https://www.youtube.com/@morgan_tate

idea of the week 💡

Credit: ideabrowser.com

DoorLog - the decision registry for SMB operators

• Problem: small business owners make one-way door decisions (price cuts, key hires, partner splits, leases) with zero process. The reasoning lives in gut feel and text threads, and the cost shows up 18 months later when nobody can explain why the margin died. Come exit time, buyers price that chaos straight into the offer.

• Idea: a lightweight decision registry. Log the decision, the one-sentence goal, a reversibility rating (one-way or two-way door), and a scheduled review date. The tool nags you to review the outcome, so your judgment actually compounds instead of resetting every quarter.

• How it works (wedge): start as a simple template plus email/Slack nudges. Sell through business coaches and EOS implementers who already force quarterly reviews and need somewhere for decisions to live. The review-date reminder is the retention hook.

• How it makes money: $29/month per owner, $99/month for leadership teams, and a white-label tier for coaches who bundle it into their practice.

• Why it might fail: journaling tools die from disuse. The owners who need it most are the least likely to document anything, and behaviour change, not software, is the real product.

my two cents: buyers pay premiums for businesses where the thinking is on paper instead of in the owner’s head. A decision log is scar tissue you can show in diligence. Anything that turns gut feel into documentation is worth real multiple points at exit.

workouts this week

at-home

14-minute AMRAP:

• 10 push-ups

• 20 walking lunges

• 12 sit-ups

• 30-second plank

gym

Strength + conditioning. 5 rounds:

• Bench press: 6 reps (moderate-heavy)

• Romanian deadlift: 8 reps

• Pull-ups: 8 reps (band if needed)

• Assault bike: 40 seconds hard

Rest 2 minutes between rounds.

outdoors

• 10-minute easy jog (warm-up)

• 5 rounds: 2-minute run (steady-hard), 1-minute walk (recover)

• 10-minute walk (cool-down)

tweet of the week

Clip breaking down the 1-way vs. 2-way door framework:

my plugs

• Schedule a confidential call to discuss selling your business.

• Book your free Exit Audit: We guarantee we’ll find hidden profit in your business. Start here →

• Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater’s new deal portal HERE

• Download a FREE copy of my Million Dollar Business Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

Thinking about selling your business?

A confidential, no-pressure conversation about what your business is worth and what a sale would actually look like. Schedule a call →

put your oxygen mask on first

The worst day of my entrepreneurship career was laying off the team of my failed startup.

In a moment of post-mortem reflection, I realized the horrific irony. Had I simply taken care of myself first, I could have prevented hurting the rest of the team.

Because if you don’t take care of yourself first, it’s easy to suffocate while trying to help everyone around you.

Side note: this is a bit of an insane topic to write about as I’m about to board an international flight but yolo.

Over the past decade I’ve had the misfortune of building multiple companies at once. It sounds impressive, but it’s a curse.

There’s a saying in start-ups: starting a company is like throwing the pieces of an airplane off a cliff and assembling it on the way down (another airplane analogy - nice).

If that wasn’t challenging enough, at my previous start-up we threw all the parts off the cliff -except we didn’t even have a complete plane in the mix. We had parts from four different planes, and as we plummeted, we scrambled between the four piles trying to build them all at once.

Spoiler: none were a success.

Even worse, we had real early traction with 1 of the 4 projects, but figured there were greater riches elsewhere and lost all focus. The core idea (helping business owners sell their business more easily) was the winner, and it’s what we do at Breakwater today. But it conflicted with another one of our projects, so instead of doubling down, we kept reinventing the wheel and launching new ideas.

The team felt it worst. They were constantly whipped into new ideas and new directions, never given the chance to master their craft. How frustrating.

It’s the same as fad diets and workout trends. Everyone gets excited by the new idea, but not by the strategy that actually works: doing the thing with traction, every day, for decades.

The greatest form of self-improvement is compounding daily discipline across a lifetime. But there’s a strange paradox in how entrepreneurs relate to discipline. On one hand, we’re some of the hardest working people alive, with decades of sacrifice to show for it. On the other, shiny object syndrome makes us incapable of focusing on the ‘boring stuff’ that actually drives success.

So put your own mask on first. Protect your health, your focus, and the one plane worth building. You can’t help anyone if you’re the one gasping for air.

idea of the week 💡

Credit: ideabrowser.com

Winpick — the launch and distribution service for indie Windows tools

• Problem: solo Windows developers build the tools power users love (think: a clipboard manager that beats the paid one), then hit a discovery wall. GitHub pulls stars but not one paying user, a Reddit post dies inside an hour, and direct downloads trip a SmartScreen warning that kills trust on sight. The Microsoft Store lists ten thousand tools and surfaces none — a good app drowns beside dead ones.

• Idea: a curated first-customer channel. Winpick hand-reviews each submission on a clean machine, publishes a demo page with an install walkthrough and a plain-English description, and sends three to five vetted tools per week to IT admins and power users who actually pay for Windows software. Curation is the product.

• How it works (wedge): hand-pick twenty solid tools from GitHub, indie forums, and Show HN. Test each on a fresh Windows install and write plain descriptions. Launch the newsletter on Beehiiv, seeding subscribers from r/Windows11, r/sysadmin, and power-user forums. Run the first issues free, then charge for a featured spot once open rates hold.

• How it makes money: $99 buys a developer a launch package with a listing and a written review, $10/month keeps them visible between launches, and a 10% cut on each sale Winpick sends ties revenue straight to a developer's real outcome.

• Why it might fail: trust is the whole business. It takes months to earn and one bad pick undoes ten good ones. Monetization from a small developer supply side is unproven, and the editorial workload doesn't scale without diluting the very curation that makes it valuable.

Reply to everything. Edit nothing.

Your inbox is full. Slack is piling up. Client messages need a response yesterday. Typing thoughtful replies to all of it takes hours you don't have.

Wispr Flow turns your voice into clean, professional text you can send the moment you stop talking. Speak like you would to a colleague — tangents and all — and get polished output. Emails, Slack, LinkedIn, WhatsApp, whatever's open.

89% of messages sent with zero edits. Used by teams at OpenAI, Vercel, and Clay. Works on Mac, Windows, and iPhone.

Try Wispr Flow free

workouts this week

at-home

16-minute AMRAP:

• 10 burpees

• 15 air squats

• 10 push-ups

• 40-second wall sit

gym

Strength + conditioning. 5 rounds:

• Front squat: 5 reps (moderate-heavy)

• Incline dumbbell press: 10 reps

• Barbell row: 8 reps

• Ski erg or assault bike: 45 seconds hard

Rest 2 minutes between rounds.

outdoors

• 10-minute easy jog (warm-up)

• 8 rounds: 30-second sprint, 90-second walk (recover)

• 10-minute walk (cool-down)

new videos on youtube

I am back to (try) and post more regularly on YouTube focused on buying & selling businesses. If that's of interest, make sure to subscribe:

Morgan Tate

CEO at Breakwater M&A - unlocking life-changing exits for hardworking entrepreneurs. We've closed $250M+ in deals for owners of $2M–$20M businesses, and this channel is where I show you how it actually works: what your business is really worth, how deals get done (and fall apart), what buyers look for, and the strategies that add six or seven figures to your exit. You'll also get a behind-the-scenes look at building Breakwater - an AI-native M&A firm - plus my review of business deals across North America. Curious what your business is worth? Take our free, confidential Exit Audit: breakwaterma.com New videos every week. Subscribe and don't leave money on the table for your exit.

YouTube

tweet of the week

Moses Kagan on the tunnel you enter at ~15 that shoots you out at ~35 — and how much of the rest of your life is determined by the choices you make (and the luck you have) inside it.

— # (#)

my plugs

• Schedule a confidential call to discuss selling your business.

• Book your free Exit Audit: We guarantee we'll find hidden profit in your business. Start here →

• Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater's new deal portal HERE

• Download a FREE copy of my Million Dollar Business Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

Thinking about selling your business?

A confidential, no-pressure conversation about what your business is worth and what a sale would actually look like. Schedule a call →

You know those people that seem good at everything?

The ones that came first in track & field in elementary, the straight A honour roll student, the type that gets a cool consulting job after college - you know the type.

I wasn’t one of those people. Winning seemed elusive and was always just out of reach.

For example, there were a lot of #17 place cross country ribbons in my room. There was an overwhelming amount of silver medals from rugby (I would eventually start tossing them in the trash).

I did an internship at a wealth management firm one summer in University for $5/hour in exchange for a higher commission. This bet on myself was a failure - I made almost $0 all summer. The saving grace was landing one “big” commission that arrived 1-week before next semester’s tuition was due (with no back-up plan).

I took on a risky job at a start-up with a significant salary cut for the promise of future equity. The founder dragged out that equity promise for 2 years, then delivered a humiliating low-ball % offer. So bad that I immediately quit.

My previous start-up, DealBuilder, went through more pivots than Dalmatians, while my other start-up friends reached dazzling valuations, exits, and growth. The saving grace? Receiving acquisition interest from the biggest player in our industry, only for the deal to die at the last minute.

While I was never last, I always felt second best. And, as a wise man once said, “if you’re not first, you’re last.” Or as my gym teacher put it, “2nd place is the 1st loser.”

There is a sentiment in sports that it’s better to win bronze than get silver. Bronze feels like a win. Silver feels like proof that someone stood exactly where you wanted to stand. While true, to a certain degree, there is no greater fire than a competitor in the face of suffering:

“I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games… I’ve failed over and over and over again in my life. And that is why I succeed.”

• Michael Jordan

That quote is overused, but c’mon it’s so good. Especially when anyone over 40 has some sort of amnesia where they forgot that Michael Jordan actually missed a shot or two.

Now, I ain’t no MJ (I don’t gamble). But I have learned that success is sweeter on the other side of failure.

As I’ve previously written, I lived a strange double-life when it came to genetics. Until the age of about 15 - I was the smallest guy on any sports team. Not only that, I was slow and weak (picture: Diary of a Wimpy Kid).

This spurred a small man complex rivalling that of Napoleon. On the rugby field I would pick fights with the biggest guys, never stay down if I was hurt, and was always proving “them” wrong. Whoever “they” were.

To the surprise of everyone (including “them”), I would go on to add about 100 lbs and grow a foot between grade 10 and 2nd year University. For the first time in my athletic life, I was playing on a level field and the impact was immediate.

Ironically, all those years of playing a physical sport (rugby) undersized had given me an upper-hand vs the men who grew up as the biggest kids. They had never needed technique, because size did the work for them. I had needed technique to survive. The years of coming middle of the pack also gave me a work ethic that had faded from the 1st place cross country kids decades ago.

It has been the same experience since starting Breakwater. Experienced founders talk of the clarity the ‘second go round’ gives you as an operator and this has been my experience. Having been through the struggle of a failed start-up, decision making is easier and our growth has been 10x faster.

I see the same thing on the sell-side every week. The owners who get the cleanest exits are almost never the ones who had a smooth ride. They’re the ones who survived a bad customer year, a lawsuit, a partner split, a season where payroll was a coin flip. That scar tissue shows up in diligence as calm. Buyers can smell it.

The founders who’ve never been punched in the mouth are the ones who blow up over the first re-trade.

Don’t get me wrong, it has still been hard. But for what the inexperienced traveller calls plight, the wise traveller identifies as the journey.

As an entrepreneur it’s easy to feel like the first loser. To be honest, there are a lot of days that will make you feel just like a loser lol. Remember we have seasons, and winter makes us appreciate when the sun warms our skin.

So keep the landfill of silver. One day it’ll be the most valuable thing you own.

new videos on youtube

I am back to (try) and post more regularly on YouTube focused on buying & selling businesses. If that’s of interest, make sure to subscribe: https://www.youtube.com/@morgan_tate

idea of the week 💡

Credit: ideabrowser.com

Rebato - the unclaimed money map for new parents

• Problem: new parents qualify for thousands of dollars that nobody hands them. Benefits are scattered across state programs, hospital giveaways, brand boxes, diaper banks, and tax credits, each on its own site with its own deadline. Sleep-deprived parents open a dozen tabs and still miss half of it. The money expires in the gap between qualifying and finding out.

• Idea: two inputs, a zip code and a due date, load a map of everything a family qualifies for. Each program is tagged with its deadline and the steps to claim it. Benefit-finder apps exist for defined groups like military families, but none map the local programs a new parent qualifies for. Generic guides repeat the same twenty national listings. Rebato surfaces the forty local ones you can actually claim before they expire.

• How it works (wedge): map three high-value states first (California, New York, Texas). Pull the top fifty programs per state into an Airtable backend from government databases and registry pages. One short form takes zip code, due date, and income range, then filters the list down to one family. Ship it to twenty parents in test markets and watch what they click, claim, and share. Expiration alerts are the feature that pulls a parent back next month.

• How it makes money: $8/month for early access with full filtering and alerts, $15/month for Parent Plus with community-verified updates and a heads-up when a new program opens nearby. Sponsored placement from baby brands adds revenue without touching the subscription price. Distribution rides where parents already gather: Facebook groups, r/BabyBumps, and TikTok creators filming their benefit hauls.

• Why it might fail: keeping listings current is the whole business. A benefit with a dead deadline is worse than no listing at all. Community engagement is obvious, monetization is unproven, and parents are a notoriously cheap subscription market.

workouts this week

at-home

12-minute EMOM (every minute on the minute), alternating:

• Minute 1: 15 push-ups

• Minute 2: 20 air squats

• Minute 3: 30-second hollow hold

gym

Strength + conditioning. 5 rounds:

• Deadlift: 5 reps (moderate-heavy)

• Dumbbell bench press: 10 reps

• Chin-ups: 6 reps (band if needed)

• Farmer carry: 40 metres heavy

Rest 2 minutes between rounds.

outdoors

• 10-minute easy jog (warm-up)

• 6 rounds: 60-second hill sprint, walk down to recover

• 10-minute walk (cool-down)

tweet of the week

my plugs

• Schedule a confidential call to discuss selling your business.

• Book your free Exit Audit: We guarantee we’ll find hidden profit in your business. Start here →

• Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater’s new deal portal HERE

• Download a FREE copy of my Million Dollar Business Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

Take the 7-Day Founder Fitness Challenge

Seven days of short workouts to kickstart your own daily streak. Start here →

You’ll hear people talk about how ‘easy’ high school or University was.

Or you’ll hear stories from successful entrepreneurs who were ‘too busy with side hustles’ to attend class or study, which is why their grades sucked. Or they had ADHD or dyslexia (who doesn’t these days), to explain their GPA.

I was NOT that guy.

I was the guy who studied HARD and still walked out with a C, D, or F. Now don’t get me wrong, I managed a few A’s, but they were in classes that came naturally to me like English, History, or… PE (a real intellectual combo). Math and Science? Didn’t matter how much studying I did — I was sweating come test time.

Turns out, it’s not because I’m stupid. It’s because I wasn’t thinking like a dumbass (stay with me).

Like the midwit meme, I (the midwit) would white-knuckle my way through studying, especially in math. I’d try to memorize how to do the practice questions instead of learning how to solve the problem. The moment the test had any variance from the practice exam — I was lost. If I’d simplified my approach instead of complicating it, I would’ve been fine.

There’s a joke in the entrepreneurship community that real estate has the highest net worth-to-lowest IQ ratio (to be clear, this is not my joke). Real estate guys get this rep because the entire playbook is: buy a building collecting $X of rent per month, pay a $Y/month mortgage, pocket $Z in profit. Then hold it for decades while the rent pays down the mortgage, and eventually sell it for a big gain or pass it along to the family.

Now, if you reacted to that with “hey, it’s not that simple!” — congratulations, you’re approaching it like a midwit. Because it really is that simple. Executing it is not.

I’ve witnessed this countless times. You meet a wildly successful entrepreneur who, respectfully, seems like a complete dumbass. But that’s exactly the point. They never overcomplicated their way out of a good decision.

A lot of people come to Breakwater to buy a business. Unfortunately, we deal with a lot of midwits. These are the buyers hunting the perfect ‘unicorn’: low CAPEX, a full-time CEO already running the place, and an owner with ‘no other options’ who’ll take $0 down. In the midwit fantasy, the dividend cheques start rolling in month one while they ride off into the sunset of their passive income oasis.

The result? They never find anything that ticks every box, get frustrated, and quit their search without ever buying anything. Meanwhile, the best acquisition entrepreneurs (and that dumbass at the cocktail mixer) don’t overthink it. They buy a cash-flowing business for a fair price, make a few small tweaks, and let it compound for decades.

So the next time something looks ‘too simple,’ remember: while the midwits are busy building spreadsheets to prove it can’t work, some delighted dumbass is already living off it.

new videos on youtube

I am back to (try) and post more regularly on YouTube focused on buying & selling businesses. If that’s of interest, make sure to subscribe: https://www.youtube.com/@morgan_tate

idea of the week 💡

Credit: ideabrowser.com

ExitBrain — an AI exit interview that pulls the business out of the owner’s head

• Problem: 70%+ of small businesses listed for sale never sell. the three usual culprits: too much owner dependence, messy financials, unpredictable revenue. a retiring boomer and his son on r/smallbusiness just ran a $374k/yr business through meeting after meeting and still couldn’t get it sold. the operating manual was never written down — it lives in one guy’s head, and buyers won’t pay a premium for a head.

• Idea: an AI interviewer that asks the owner exactly what a buyer’s diligence team would ask, then turns the answers into an interactive playbook a stranger could run the business from. answer the objections and the rejections upfront instead of discovering them in week six of diligence.

• How it works (wedge): structured voice sessions ask the buyer questions — which ten clients actually matter, what breaks in February, who has the vendor relationships, what happens when you’re gone for three weeks. transcripts compile into SOPs, an org map, a client concentration view, and a risk list. a refresh session re-interviews the owner every quarter as staff and pricing drift. start with brokers and exit planners who already have listings that keep dying in diligence.

• How it makes money: $499 per interview, $99/month to keep the playbook current. real upside is the channel — brokers, M&A advisors, and QoE providers white-labelling it as a pre-listing step, plus the data asset that comes from thousands of owners describing how their businesses actually run.

• Why it might fail: the people who need it most are the least likely to buy it — owners who won’t document anything also won’t sit for six hours of interviews. and a playbook doesn’t fix messy books or lumpy revenue, so the promise of “add dollars to the offer” is hard to prove. feasibility 7/10 — the tech is straightforward, the behaviour change isn’t.

my two cents: this is the deal I see die most often. the business is fine, the owner is the business, and the buyer prices that risk right into the offer. anything that moves knowledge from the owner’s head onto paper before a listing goes live is worth real multiple points.

workouts this week

at-home

15-minute AMRAP:

• 12 push-ups

• 16 walking lunges

• 12 backpack (or dumbbell) rows

• 30-second plank

gym

Strength + conditioning. 4 rounds:

• Back squat: 6 reps (moderate-heavy)

• Strict overhead press: 8 reps

• Pull-ups: 8 reps (band if needed)

• Row erg: 45 seconds hard

Rest 90 seconds between rounds.

outdoors

• 10-minute easy jog (warm-up)

• 4 rounds: 3-minute run (steady-hard), 90-second walk (recover)

• 5-minute walk (cool-down)

tweet of the week

I built an entire startup around the idea of outworking and outsmarting everyone in the industry… spoiler: it failed.

my plugs

• Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater’s new deal portal HERE

• Book your free Exit Audit: We guarantee we’ll find hidden profit in your business. Start here →

• Schedule a confidential call to discuss selling your business.

• Download a FREE copy of my Million Dollar Business Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

“What would you like to be when you grow up?”

My grade 3 teacher asked me this, and I responded, “A cartoonist.”

She replied, “It will be hard to make money doing that.”

To which I replied, “Well, the creator of The Simpsons was a cartoonist, and he has lots of money.”

There was no rebuttal from my teacher.

You see, from a young age I’ve had delusions of grandeur. Many entrepreneurs are wired the same way. It’s a side benefit of our mental predisposition. But here’s what I’ve learned since grade 3: the dream isn’t the hard part, protecting it is.

When I was 13, Robert Emsie (Canadian 100m gold medal sprinter) spoke to our class about ‘Dream Killers’: people in your life, sometimes even with good intentions, who always put a damper on your dreams.

Dream killers often defend themselves by stating they’re realists, or that they’re protecting you from future disappointment, when really they’re just limiting your future potential.

Having spent the last decade building companies, I’ve met an unfortunate reality: I’ve faced just as many, if not more, dream killers in adulthood than I did as a child. Often bitter from years of corporate captivity, these people are the first to find glee in the failure of their entrepreneurial friends, or to come up with 101 reasons why an idea won’t work.

For example, I was recently at a dinner party where one of the guests said they would love to start a company, but “all the good ideas have already been done.” It was one of the most depressing statements I’ve heard in a while, especially given we’re living through arguably the most exciting time in human history across multiple industries: space, longevity, and AI.

But here’s the uncomfortable part: the biggest dream killer for most of us doesn’t sit across the dinner table. It resides within. We tell ourselves stupid phrases like “in another lifetime” or “if only I had X — then I could afford to do Y.”

My own aspirations of building a cartoon empire have changed, but my propensity to dream has not. These days, the dream is building a global financial services business (Breakwater)… the 8-year-old cartoonist inside me just shook his head and muttered “sellout” 😂 😂

When I look back at the ledger of life, I’d rather stand on the side of ‘dreamer’ than ‘dream killer’. Most of us would.

So maybe I’m delusional. Maybe I’m missing the plot. But every company, every breakthrough, and every cartoon empire started as somebody’s delusion of grandeur. The teacher, the dinner guest, the voice in your own head — none of them get a vote unless you give them one. Guard your delusions.

The world has more than enough realists, and not nearly enough cartoonists.

Access My Idea Vault (75 business ideas)

75 validated business ideas, pulled straight from this newsletter.

Download the full Idea Vault for FREE HERE

idea of the week 💡

Credit: ideabrowser.com

GMBVault — a backup and evidence vault for Google Business Profiles

• Problem: local businesses live and die by their Google Business Profile. a competitor flag, a bot review attack, or an unexplained suspension can wipe one out overnight — and owners end up digging through old screenshots to build appeals that go unanswered.

• Idea: automated backups of everything on a profile — reviews, photos, Q&A, replies, posts, hours, categories — plus full-page screenshots. dated snapshots live in a private vault, so when disaster hits, there’s a clean evidence packet with one-click export for appeals. agencies get one dashboard to track backup status across every client location.

• How it works (wedge): a scraper pulls listing data into timestamped records, browser automation captures the screenshots, and weekly crawls flag disappearing reviews or sudden rating shifts. ship it to ten local owners currently stuck in review disputes and grow from there.

• How it makes money: $29/month for a single location (weekly backups + alerts), $99/month for agencies with the consolidated dashboard. distribution through local search communities and the GBP forums where suspension horror stories surface daily. retention follows the insurance model — boring until disaster, irreplaceable after.

• Why it might fail: Reputation.com already monitors reviews (though it skips the dated evidence trail), and the whole product rides on scraping Google’s interface. feasibility sits at 6/10 — moderate build, 2–4 week MVP.

workouts this week

at-home

• 20-min AMRAP: 10 push-ups, 15 air squats, 10 sit-ups, 45 sec high knees

gym

• 5 rounds: 5 deadlifts (heavy but clean), 10 DB bench press, 15 cal row — rest 90 sec between rounds

outdoors

• 35-min run: 5-min warmup, 6 × (2 min hard / 2 min easy), 5-min cooldown

tweet of the week

my plugs

• interested in buying a business? join our deal distribution list here

• need a quality of earnings (Qoe) for a business acquisition? Breakwater now offers them here

• thinking about selling? grab a free Exit Audit or book a confidential call

• download the Million Dollar Business Exit Guide

• subscribe to my YouTube channel and the Main Street Memo

• follow along on X, instagram, and linkedin

every second counts.

Take the 7-Day Founder Fitness Challenge

Seven days of short workouts to kickstart your own daily streak. Start here →

Some big personal news: I got married last week. It was the greatest day of my life (so far).

We wrote our own vows, which got me thinking about what a vow actually means. Google defines it as a solemn, earnest, and binding promise or pledge.

Sounds a bit intimidating, right? You’ll even hear the word ‘sacrifice’ used synonymously with ‘commitment’.

But this framing is all wrong.

Most people experience commitment as sacrifice because they were never actually committed to the thing they promised. They can’t commit because they:

1. Don’t believe the person on the receiving end of the promise (themselves included) is worthy of it, or

2. Don’t believe the thing they’re committing to beats the options they’d be “giving up.”

If either one is true, of course every commitment feels like a loss. Go back to Google’s definition and notice the word “earnest.” An earnest promise is one you actually mean, not one you grit your teeth through. If keeping a commitment feels like white-knuckling through Costco on a Sunday, the answer isn’t more willpower, it’s not making that commitment in the first place.

This all gets flipped on its head when you believe in both the person and the end goal. Because you’re not giving anything up. If anything, you should feel like you’re getting the best deal on Earth. That’s what marrying my wife felt like: the promised land of spending the rest of my life with her far surpasses any ‘sacrifice’ I need to make.

Now, to transition from a beautiful personal moment to talking about my business 😂 😂

We see the same pattern in M&A constantly. The sellers who suffer most through a deal are the ones who never fully commit to selling. Every diligence request feels like an invasion and every negotiation point feels like a concession, because part of them still has 1 foot out the door. The committed sellers? They move fast, negotiate clean, and sleep fine. Same process, completely different experience.

Commitment is only heavy while you’re still deciding. Once you actually choose, the weight mostly disappears. What’s left is just the work, and work you chose barely feels like sacrifice at all.

So stop conflating the two. A vow isn’t a cage. It’s the door you get to close behind you as to enter your dream state.

idea of the week 💡

Credit: ideabrowser.com

• Problem: Vet surgical practices send dogs home after knee and joint operations with generic recovery sheets. Those sheets assume calm animals, open floor plans, and owners who can lift 90 pounds. Reality: high-energy breeds in small apartments, nervous dogs refusing crate rest, and elderly owners managing alone. Callbacks spike. The protocol works inside the clinic and falls apart at home.

• Idea: Pawscript builds adaptive post-op plans for each case before the patient leaves the building. A vet tech fills out a 5-minute intake covering breed, behavior profile (crate-refusal, separation anxiety), living space, other pets, stairs, and the caretaker’s physical limits. The system generates a staged recovery plan: confinement setups sized for the apartment, enrichment routines for high-drive breeds, harness recommendations for caretakers who struggle to lift, and escalation scripts for late-night emergencies.

• How it works (wedge): Ship to 3 pilot surgical clinics doing large volumes of knee and joint procedures. Build the MVP as a Typeform-style questionnaire feeding a rules engine and template library, with breed-tagged enrichment routines and troubleshooting prompts generated from the intake’s behavior flags. Integrate with Cornerstone or ezyVet so the plan lives inside existing workflows, then track each clinic’s 30-day callback rate against baseline and refine the sections that move it most.

• How it makes money: $199 to $499 per practice per month, tiered by procedure volume. Distribution runs through veterinary surgery conferences, partnerships with rehab brands like Ruffwear and Walkin’ Pets, and word of mouth in specialist referral networks. Expansion adds a $29 direct-to-caretaker app synced to the discharge summary, plus compliance data packaged for pet insurers as a second revenue layer.

• Why it might fail: The plan has to survive contact with a 90-pound husky in a studio apartment. If clinics don’t see callback rates visibly drop, this is just a prettier discharge sheet and they’ll churn. The way through is obsessive measurement against each clinic’s baseline and ruthlessly improving the sections that actually move the number.

workouts this week

at-home

14-minute AMRAP:

• 12 push-ups

• 16 walking lunges

• 12 sit-ups

• 6 burpees

gym

Strength + conditioning. 4 rounds:

• Back squat: 6 reps (moderate-heavy)

• Push press: 8 reps

• Chest-supported row: 10 reps

• Ski erg or assault bike: 45 seconds hard

Rest 90 seconds between rounds.

outdoors

• 5-minute easy jog (warm-up)

• 6 rounds: 400-metre run (hard), 90-second walk (recover)

• 5-minute walk (cool-down)

tweet of the week

this is exactly why I write this newsletter every week

my plugs

• Apply for The Trading Post. Deal-by-deal private investment opportunities in Canadian SMEs. Apply here →

• Book your free Exit Audit. We guarantee we’ll find hidden profit in your business. Start here →

• Schedule a confidential call to discuss selling your business.

• Download a FREE copy of my Million Dollar Business Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

Take the 7-Day Founder Fitness Challenge

Seven days of short workouts to kickstart your own daily streak. Start here →

I’ve learned something very quickly in business:

Nobody wants to work with Eeyore.

You know the type.

Every idea is stupid, they see the problem in every plan. Every opportunity is “probably not worth it.” Every time someone gets excited, it’s like a wet blanket crashing through the ceiling tiles to smother everyone’s enthusiasm.

And to be clear, I’m not talking about thoughtful skepticism.

Good operators/investors ask hard questions. Someone stress testing your ideas and assumptions is useful and necessary for a business to thrive over the long-term.

I’m talking about the person who finds a leak in the boat and then feeling smug while everyone else tries to row. Those people are miserable to hire, miserable to manage, and miserable to work with.

They drain oxygen from the room. They make simple things feel hard. They confuse cynicism for intelligence because being negative gives them the cheap high of sounding sophisticated without ever having to build anything.

It’s very easy to say why something won’t work.

It’s much harder to be the person who says, “What would have to be true for this idea to work?” That person is magnetic.

They don’t have to be the smartest or skilled because they bring the energy. They’re open to ideas and make the work lighter without making it unserious. They can sit in a stressful room and still crack a joke at the right moment.

The result is that they end up drawing people in because people want to work with them.

In my line of work (M&A) this is critical when people are making constant high-stakes decisions (this tends to get everyone wound a bit tight).

For most (except those pesky trust funders) we spend most of our lives working. That’s insane when you actually think about it. Decades of calls, emails, meetings, negotiations, losses, wins, problems, clients, hiring, firing, and trying again. Why would you want to do all of that with people who make every day feel worse?

I’d rather be around the person who brings a little joy. Serious about the mission, but not addicted to unnecessary self-torture. That’s what I mean by being magnetic.

So be magnetic, the world has enough Eeyores.

Get started with our 7-day challenge

Seven days of short workouts + entrepreneurial challenges kickstart your own daily streak of personal progress → Start here

blog of the week

Seller Due Diligence Checklist: What Business Owners Need Before Going to Market

If you’re thinking about selling your business, diligence is not something that starts after a buyer shows up.

It starts before you go to market.

The more prepared you are, the fewer surprises show up later. Clean financials, organized contracts, clear customer data, employee documentation, tax records, and a defensible story around the business all help protect momentum once a deal is live.

The goal is simple: reduce buyer uncertainty before it becomes a price chip.

Read the full checklist here: Seller Due Diligence Checklist →

idea of the week 💡

Credit: ideabrowser.com

• Problem: Schools keep adding software tools one app at a time. A classroom video app autoplays the next clip. A math app uses streaks. A quiz tool adds social pressure. Another platform pushes notifications all day. Each product may look harmless in isolation, but stacked across a student’s day they create a cumulative attention burden nobody is really measuring.

• Idea: Cumula is an attention audit for school software stacks. It scores the full portfolio of classroom apps and shows administrators how autoplay, streaks, notifications, variable rewards, and social mechanics compound across the school day. Leadership gets a defensible report, a portfolio score, and a procurement gate for evaluating new apps before signing another contract.

• How it works (wedge): Start with three school networks and manually audit their software stacks at $10K each. Use public per-app ratings from sources like Common Sense Media, then add the missing layer: how attention mechanics interact when students encounter them across multiple tools in the same day. Turn that into a burden score per student per day that leadership can act on.

• How it makes money: The initial manual audit lands the account. The ongoing scorecard and procurement gate renew annually at roughly $15K, scaled by stack size. Buyers are reachable through education leadership groups, procurement cycles, and conferences where district technology decisions get made.

• Why it might fail: The rubric has to feel credible. If administrators see it as hand-wavy wellness theatre, it won’t survive budget scrutiny. The path through is tight methodology, clear case studies, and outcomes schools already care about: lower screen time, cleaner renewals, and fewer complaints from parents and teachers.

workouts this week

at-home

10-minute EMOM:

• Minute 1: 12 push-ups

• Minute 2: 18 air squats

• Minute 3: 12 sit-ups

• Minute 4: 8 burpees

• Minute 5: Rest

Repeat twice.

gym

Strength + conditioning. 5 rounds:

• Front squat: 5 reps

• Pull-ups or lat pulldown: 8-10 reps

• Dumbbell bench press: 10 reps

• Farmer carry: 40 metres

• Row erg: 250 metres hard

Rest 90 seconds between rounds.

outdoors

• 5-minute easy jog

• 8 rounds: 30-second hill sprint, walk back down

• 5-minute walk cool-down

my plugs

• Apply for The Trading Post. Deal-by-deal private investment opportunities in Canadian SMEs. Apply here →

• Book your free Exit Audit. We guarantee we’ll find hidden profit in your business. Start here →

• Schedule a confidential call to discuss selling your business.

• Download a FREE copy of my Million Dollar Business Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

Take the 7-Day Founder Fitness Challenge

Seven days of short workouts to kickstart your own daily streak. Start here →

To live any life worth living, we must learn to love suffering.

The concept is strange, but there is joy that shows up when you choose to do hard things on purpose. The simplest way I can explain it is the cold water effect.

Jumping into a cold lake for no reason just sucks. But picture a long summer hike to a mountaintop lake. You sweat through your clothes, swat away bugs, and by the time you reach the top you’re dusty, hot, and worn out. Then you see the water. Relief washes over you before you even dive in, and when you do, it feels incredible. The effort is exactly what makes it worth it, and that contrast is the whole point.

That’s the upside of voluntary discomfort, and the Stoics understood it better than most people do today. Every time you push through something hard, you prove the doubting voice in your head wrong, and that proof gives you the resolve to take on something bigger next time. But the acceptance of suffering is a double-edged sword.

The trap is turning struggle into your whole personality. You start chasing discomfort for its own sake and never let yourself feel good about anything. Like a dopamine-starved masochist, you never congratulate yourself. You wear “toughness” like a badge and call it virtue, when really it’s just fear that if you stop to pat yourself on the back, you might stop moving forward.

But even the Stoics, the original advocates for hard things, never confused suffering with virtue. Seneca put it plainly:

“We suffer more often in imagination than in reality.”
Seneca, Letters from a Stoic

Most of the pain we carry isn’t the work itself, it’s the story we pile on top of it. Stoicism was never about chasing pain. It’s about choosing the right pain: the kind that buys freedom, builds competence, and makes the next version of you more resilient. Everything past that is suffering you manufactured.

Stoicism also teaches us to focus only on what we can control. The ‘struggle’ that comes with chasing a hard goal is unavoidable. But the extra layer of self-punishment, the refusal to ever feel good, is a choice. Choosing to live in needless misery when you don’t have to isn’t admirable. It’s foolish.

And if you never celebrate progress, you end up on the same hamster wheel entrepreneurs love to mock corporate people for running on. Ironically both groups end up in the matrix: perpetual suffering with no pay-off.

To make a long point short: celebrate the small wins. You don’t need to throw a party every time you accomplish something—but give yourself some grace and a pat on the back from time to time, for heaven’s sake.

Get started with our 7-day challenge

Seven days of short workouts + entrepreneurial challenges kickstart your own daily streak of personal progress → Start here

idea of the week 💡

Credit: ideabrowser.com

• Problem: Small medical and dental clinics waste a ridiculous amount of time doing insurance benefit checks the same way giant hospitals do. Front desk staff call payers, sit on hold, fight automated menus, and try to decode coverage details one patient at a time. A 1 to 5 provider clinic can burn 10 hours a week here. Every missed or sloppy check risks a denied claim worth $200 to $2,000.

• Idea: Donedial is a voice agent that runs pre-visit benefit confirmation end to end. Staff drop patient and plan details into a dashboard, the agent calls the insurer, navigates the menu tree, handles the hold time, and returns a clean breakdown in a few minutes. Coverage status, expected out of pocket costs, and red flags that trigger denials show up as structured output before the appointment.

• How it works (wedge): Start with one payer. Reverse engineer the IVR paths, build the calling layer on a live voice API, and make the product earn its keep by absorbing waits, drop calls, and changing menus. Use transcription plus an LLM to turn messy spoken answers into structured fields. Run pilots with a handful of offices, validate against manual checks, then expand payer by payer. Each new payer adds data and increases accuracy.

• How it makes money: $200 per provider per month. One prevented denial pays for the tool. Distribution is office manager Facebook groups, billing community forums, and partnerships with practice management platforms like Dentrix and Eaglesoft.

• Why it might fail: Accuracy is everything. If the output feels unreliable, clinics will go right back to humans on the phone. The only way through is tight scoping, relentless validation, and building a dataset payer by payer instead of pretending you can cover the entire insurance world on day one.

workouts this week

at-home

12-minute AMRAP:

• 10 push-ups

• 15 air squats

• 10 sit-ups

• 8 burpees

gym

Strength + conditioning. 4 rounds:

• Trap bar deadlift: 6 reps (moderate-heavy)

• Dumbbell incline press: 10 reps

• Chest-supported row: 10 reps

• Assault bike: 45 seconds hard

Rest 90 seconds between rounds.

outdoors

• 10-minute easy jog (warm-up)

• 5 rounds: 2-minute run (hard), 1-minute walk (recover)

• 5-minute walk (cool-down)

tweet of the week

used this life hack in many times

my plugs

• Apply for The Trading Post. Deal-by-deal private investment opportunities in Canadian SMEs. Apply here →

• Book your free Exit Audit. We guarantee we’ll find hidden profit in your business. Start here →

• Schedule a confidential call to discuss selling your business.

• Download a FREE copy of my Million Dollar Business Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

Take the 7-Day Founder Fitness Challenge

Seven days of short workouts to kickstart your own daily streak. Start here →

If you’re like me, you’re perpetually dissatisfied.

The bar you set for your own life rises at an impossible rate. You’re a high-jumper trying to leap into the basket of a hot-air balloon as it lifts off.

It’s a constant desire to be the best version of yourself, an unrelenting ambition that keeps you in a state of permanent discomfort with the status quo. This plague affects almost every entrepreneur I know.

And despite what sounds like a tortuous existence, I wouldn’t have it any other way.

Why? Because this state is self-imposed, not caused by anyone else. That distinction is where most people get it wrong.

All our lives, we’re told not to compare ourselves to others, which is harder than ever in the age of social media. Every other day I see another 14-year-old who built an AI app that did $10M in revenue in four months. At some point, the internet became a house of mirrors, and the reflection gets more horrific at every turn.

Is that $10M even real? Who cares. Say it is. What does it actually change about my life, other than making me (a 30-year-old) feel behind? I have zero context on their life. Maybe they feel behind because of the 6-year-old making $11M/year reviewing toys (yes, real).

The point: there’s a healthy level of restlessness, especially if you’re a creative or an entrepreneur. Constant dissatisfaction is a feature, not a bug. The trouble starts when that unhappiness comes from keeping up with the Joneses instead of pursuing your own Personal Legend.

“Ambition means tying your well-being to what other people say or do. Sanity means tying it to your own actions.” Marcus Aurelius, Meditations

So don’t let that restlessness go to waste. Pour it into the one thing you actually control: action toward your own goals.

Action your goals with this 7-day challenge

Seven days of short workouts + entrepreneurial challenges kickstart your own daily streak of personal progress → Start here

idea of the week 💡

Credit: ideabrowser.com

• Problem: Estate planning firms close the deal, then lose control of what happens next. Clients walk out with vague instructions to retitle accounts and update beneficiaries, procrastination sets in, and 60% of signed trusts go unfunded because nobody tracks which files are complete and which sit dormant. When someone dies with an empty trust, the firm wears the liability.

• Idea: Trustwake is the post-signing execution layer for estate planning firms. Upload a signed trust plan and the system generates an asset-specific task list: retitle the brokerage account, record the deed, update the retirement-account beneficiary, move the rental property into a holding company. Clients get reminders on a set cadence, financial advisors get handoff instructions, proof-of-completion uploads are tracked per asset, and the firm sees a real-time dashboard showing which files have gone cold.

• How it makes money: $199/month per firm based on client volume, with $49 per-workflow pricing for smaller practices. One case study on improved funding-completion rates opens the door to estate-planning attorney associations and continuing-education webinars, the rooms where firms compare notes on liability. Compliance analytics and advisor-collaboration modules follow once the core workflow proves it moves trusts from signed to funded.

• Why it might fail: If the task logic feels generic, trust breaks. Specific instructions matter more than generic reminders, and deadline pressure from the attorney matters more than nudges from software. The wedge: shadow an attorney through five signings, map every asset-transfer task that follows, run it on a shared Airtable with automated email reminders, then test proof-of-completion uploads with 3 clients per firm before productizing.

workouts this week

at-home

12-minute AMRAP:

• 10 push-ups

• 15 air squats

• 10 sit-ups

• 8 burpees

gym

Strength + conditioning. 4 rounds:

• Trap bar deadlift: 6 reps (moderate-heavy)

• Dumbbell incline press: 10 reps

• Chest-supported row: 10 reps

• Assault bike: 45 seconds hard

Rest 90 seconds between rounds.

outdoors

• 10-minute easy jog (warm-up)

• 5 rounds: 2-minute run (hard), 1-minute walk (recover)

• 5-minute walk (cool-down)

tweet of the week

I don’t do public math, that’s a private matter 😂

my plugs

• Apply for The Trading Post. Deal-by-deal private investment opportunities in Canadian SMEs. Apply here →

• Book your free Exit Audit. We guarantee we’ll find hidden profit in your business. Start here →

• Schedule a confidential call to discuss selling your business.

• Download a FREE copy of my Million Dollar Business Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

I finally read The Alchemist by Paulo Coelho recently (way behind the trend on this one), and it lived up to the hype. The story follows a shepherd chasing what Coelho calls a “Personal Legend”, his answer to the slippery question of what you’re actually meant to do with your life. What stuck with me wasn’t the romance of chasing the dream, which is the part entrepreneurial circles love to romanticize. It was how easy it is to ignore that calling and never even notice it slipping away.

Most people I meet aren’t short on ideas. If anything, they have too many. Bubbling with excitement, they will describe the entire business plan over coffee, and then go home and never touch any of it. The idea was never the issue. They just never decided it was theirs to actually build.

Paulo’s philosophy is that the universe doesn’t punish you for playing it safe; it just stops helping. Life’s hints toward your Personal Legend get harder to read, your days blur together, and one morning you wake up with a perfectly reasonable life that doesn’t feel like yours. Nothing significant goes wrong, you just stopped listening to the signs.

I’ve been thinking about this a lot this year, mostly because I’ve been trying to do the opposite. In the past, it felt like I had 16 different Personal Legends. So in 2026, I made a commitment to “excellence”: to build the best M&A firm in the world and help business owners make the most important decision of their professional lives.

In the book, the main character encounters multiple struggles in his journey. I find many people view obstacles as a barrier to their goals, when it really indicates you’re on the right path. Achieving anything meaningful requires struggle, it’s why finishing a marathon is more fulfilling than walking a mile.

Despite Breakwater being only a year old, we’ve already had our share of struggles. Deals have died at the 11th hour of diligence, a client back-tracked on a signed agreement (fun times), and we’ve had stretches where nothing seemed to go right. The shepherd in The Alchemist hits the same kind of walls. He gets robbed, loses everything more than once, and questions whether his Personal Legend is even worth chasing, right up until he realizes that every one of those setbacks was quietly teaching him something he needed for the next leg of the journey.

That’s the part that stuck with me most as an entrepreneur. The barriers weren’t the universe telling him to quit. They were the universe nudging him in the right direction, one painful lesson at a time. Building anything worthwhile works the same way. The dead deals, the broken agreements, the months from hell, none of them are detours away from your Personal Legend. They’re the road to it.

So if you’re deep in the messy part right now, take it as proof you’re actually on the path, and keep walking.

Free TikTok Shop Starter Guide

For a limited time, get our TikTok Shop starter resource folder, including a case study showing how we scaled from $0 to $90K/month in 90 days.

You’ll also get our creator approval guide plus a sample P&L to better understand channel profitability.

Get the Free Starter Kit

idea of the week 💡

Credit: ideabrowser.com

• Problem: Week two after knee surgery. Pain is a 7 out of 10. Discharge papers call some discomfort normal but never define normal. Online searches swing between best-case timelines and horror stories. Surgeon offices field the same anxious call every morning. One benchmark would settle it, and it sits unbuilt.

• Idea: Mendcurv is a mobile app that tracks pain levels, range of motion, and functional milestones after orthopedic surgery, then maps progress against anonymized recovery curves from patients who had the same procedure. Knee replacement patients logging daily pain scores see where they fall relative to thousands of similar recoveries by week. Ambiguous healing turns into a percentile. Week three pain at a 5 out of 10 lands in the 60th percentile. One number answers the question the discharge papers leave open.

• How it makes money: Subscriptions run $10 to $20 a month per patient for the duration of recovery. Orthopedic practices become the distribution channel because recommending Mendcurv at discharge reduces unnecessary follow-up visits and lowers inbound anxiety calls. Once the benchmark library covers knee procedures, hip replacements and spinal surgeries use the same tracking infrastructure with procedure-specific curves. Insurance partners pay to reduce complication rates. Each logged recovery sharpens the benchmarks behind it.

• Why it might fail: Health data compliance is the first architecture decision and determines the launch timeline. If early recovery curves feel generic, trust breaks. The wedge is partnering with 3 to 5 orthopedic surgeons to pilot with post-op patients, then validating benchmarks against real recovery trajectories. Collect 200 journeys in 90 days and earn the right to scale.

workouts this week

at-home

12-minute AMRAP:

• 10 push-ups

• 15 air squats

• 10 sit-ups

• 8 burpees

gym

Strength + conditioning. 4 rounds:

• Trap bar deadlift: 6 reps (moderate-heavy)

• Dumbbell incline press: 10 reps

• Chest-supported row: 10 reps

• Assault bike: 45 seconds hard

Rest 90 seconds between rounds.

outdoors

• 10-minute easy jog (warm-up)

• 5 rounds: 2-minute run (hard), 1-minute walk (recover)

• 5-minute walk (cool-down)

tweet of the week

😂 😂 😂

— # (#)

my plugs

• Apply for The Trading Post. Deal-by-deal private investment opportunities in Canadian SMEs. Apply here →

• Book your free Exit Audit. We guarantee we'll find hidden profit in your business. Start here →

• Schedule a confidential call to discuss selling your business.

• Download a FREE copy of my Million Dollar Business Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

Take the 7-Day Founder Fitness Challenge

Seven days of short workouts to kickstart your own daily streak. Start here →

There was a viral tweet (26M views!) this past week talking about Stephen Bartlett “ruining 3 days of his life” by having a few glasses of wine.

I get his main point. Alcohol wrecks sleep, spikes anxiety for a lot of people, and makes training harder. If your life is better without it, cutting it out completely makes a lot of sense.

But we’ve lost the plot when a couple drinks turns into a moral failure and a three-day recovery story. It’s the same energy as the “as a full-grown man I need a 45-minute bed-time routine so my sleep score doesn’t dip below 90%” crowd. A life designed around avoiding anything that might create discomfort.

Twitter, as usual, came out with torches and pitchforks for poor Stephen (the reaction was a bit much, honestly). But a lot of people made a great point: Stephen is about to become a parent. If a few glasses of wine cost three days of productivity, just wait until there’s a newborn.

We’ll probably remember the 2020s as the pendulum decade. Pro-vaccines to anti-vax. Liberal politics to conservative. Social media being harmless to it being a plague on society. One of these other swings is from the YOLO mindset of the 2010s to bubble boy longevity culture.

To be clear, I’m all for people taking care of themselves. But a lot of the health maximalist movement isn’t creating healthier people. It’s creating anxious people who live inside a constant internal risk calculator.

It’s building a life that’s:

• obsessed with avoiding discomfort

• terrified of any “suboptimal” input

• constantly running an internal risk calculator

• quietly anxious… all the time

Maybe it’s just me, but I’d rather be 90 having lived a full life than 105 because I avoided the sun, never traveled, and turned every decision into a spreadsheet. More than anything, it’s an argument for building personal resilience. Because you can’t live in a bubble, and we’ve literally seen what happens when people try.

COVID was the world’s biggest bubble experiment, and the mental health consequences were brutal. Human beings need friction, exposure, and a little chaos. Not because chaos is good, but because you’re supposed to be strong enough to handle it.

That’s the founder version of health. Not perfect inputs, and not a sterile life where every meal is macro-optimized and every choice is fear-based. It’s being able to show up on a random Tuesday after a late dinner, a glass of wine, and a short night of sleep, and still do the work.

Founder Fitness, for me, has always been about building that capacity and balance. The streak matters more than perfection because the goal isn’t to never drift. The goal is to return to center quickly and keep moving.

A full life requires risk: (safe) exposure to the sun, the occasional late night, traveling the world. In my opinion, sharing the odd bottle of wine with friends & family will do more for your soul than it costs your long-term health, and if you build real resilience, you get to enjoy it all without falling apart the next day.

The question isn’t “will this hurt my sleep score?” It’s “does this help me live a more fulfilling life?”

Are you running your business on incomplete numbers?

Most small business owners have financials, but few have financial clarity. There's a real difference between books that are technically up to date and books that actually tell you what's going on in your business right now. When accounting is reactive — updated when there's time, reviewed at tax season — you lose visibility exactly when you need it most. You can't tell which clients are truly profitable. You can't spot a cash flow gap before it becomes a crisis. BELAY's outsourced accounting team changes that.

Download the Free Guide

idea of the week 💡

Credit: ideabrowser.com

• Problem: A standard contact form returns a name and an email. The data that determines whether the deal closes sits behind twenty minutes of research the form refused to do: company size, decision-makers, recent funding, tech stack, ICP fit. The buyer typed it in. The sales team Googles it ten minutes later. The deal stalls in the gap.

• Idea: Replede replaces the contact form with an AI chat widget that runs on a single script tag. The widget asks the questions the form skipped and captures intent, budget, and timeline through a natural conversation. Behind the scenes, it enriches the lead with company size, decision-makers, recent funding, and tech stack signals so the rep calling back has a full buyer profile before the first sentence.

• How it makes money: $2,500/month for the widget + enrichment + intelligent routing. Premium at $5,000/month adds ICP campaigns plus monthly intelligence reports (tech stack changes, funding rounds, hiring signals). For mid-market B2B companies running $10K+ deals, $30K/year to replace the “we need a sales coordinator + marketing analyst” problem is an easy line item.

• Why it might fail: If the AI collects more data but the cycle time doesn’t improve, the conversation flow is wrong, not the enrichment stack. Start with five beta installs done manually, push profiles into the CRM, then iterate on which questions actually predict deal quality and speed to close.

workouts this week

at-home

12-minute AMRAP:

• 10 push-ups

• 15 air squats

• 10 sit-ups

• 8 burpees

gym

Strength + conditioning. 4 rounds:

• Trap bar deadlift: 6 reps (moderate-heavy)

• Dumbbell incline press: 10 reps

• Chest-supported row: 10 reps

• Assault bike: 45 seconds hard

Rest 90 seconds between rounds.

outdoors

• 10-minute easy jog (warm-up)

• 5 rounds: 2-minute run (hard), 1-minute walk (recover)

• 5-minute walk (cool-down)

tweet of the week

genius 😂 😂

my plugs

• Apply for The Trading Post. Deal-by-deal private investment opportunities in Canadian SMEs. Apply here →

• Book your free Exit Audit. We guarantee we'll find hidden profit in your business. Start here →

• Schedule a confidential call to discuss selling your business.

• Download a FREE copy of my Million Dollar Business Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts

Seven days of short workouts to kickstart your own daily streak. Start here →

On October 1, 2025, I committed to doing 100 push-ups and 100 squats every single day with no excuses.

In 229 days, I've missed two days. Both times I made up for it the next day by doing 200 of each.

While it started as a fitness thing. It's turned into something else entirely.

Sahil Bloom put words to it better than I could in a recent tweet. He calls it Proof of Agency. The idea is simple, if you feel stuck, pick one hard thing and do it every day for 30 days. Wake up at 5am and get into a work-out, even if it’s just push-ups and squats on your bedroom floor. It doesn't matter what the action is. What matters is that you stack 30 days of evidence that you can decide to do something and then actually do it.

Scientists call this neuroplasticity. Your brain physically rewires itself through repeated action. You stop being the person who wants to be disciplined and start being the person who is. The action proves it to you, day after day, until there's no other story your brain can tell about who you are.

I didn't know any of this when I started the 100s. I just wanted to make sure I never skipped a work-out. But the effects in other areas of my life have been wild:

• Work: I’ve also committed to sending this email every single week since Jan. 1st of 2025. After building a daily fitness commitment, keeping a weekly writing commitment has been much easier.

• Diet: I’ve been more consistent in my daily eating habits when I know that all the push-ups + squats I did that morning will go to waste with a cheat meal.

• Cooking and groceries: My cooking habits were inconsistent at best. Since implementing this daily routine, the rest of my life has fallen into a familiar rhythm and cadence.

• Sleep, focus, the boring stuff: All of these positive habits start to compound when one thing in your day is non-negotiable.

The workout itself isn't the point. The point is having one thing in your life that you absolutely will not let yourself skip, no matter what.

If you feel stuck right now, start with a simple daily commitment to yourself. Start with trying to hit a streak of 7-days, then push for a month, then a year.

To make it easier to start, I built a 7-day founder fitness challenge for exactly this reason. Seven days of short workouts designed to fit into a founder's schedule, built to give you your first stack of evidence.

Take the first step, let your brain rewire from there.

Your business has grown. Is your accounting?

If your accounting hasn't kept pace with your business, it's quietly costing you. Outdated financials, no clear view of profitability, and hours lost every week — these are growth bottlenecks, not just bookkeeping headaches. BELAY's Financial Experts handle it all.

Download the Free Guide

idea of the week 💡

Credit: ideabrowser.com

• Problem: Aging parents and the family members watching over them run a silent negotiation. The elder downplays problems to protect their independence. The family asks surface questions to avoid feeling intrusive. Both sides leave the call satisfied. Neither surfaces the thing that would actually change the care plan. An emergency eventually forces the conversation that should have happened months earlier.

• Idea: WellRing places a daily call to each senior with a warm, natural voice conversation. The AI asks how they slept, whether anything hurts, what they ate, what they have planned today. The family side gets a dashboard flagging concerning patterns: confusion, repeated complaints, mentions of dizziness or falls, mood shifts tracked over weeks. The system learns what "normal" sounds like for each person and alerts when something drifts from baseline, instead of dumping a checklist score on the family.

• How it makes money: $29.99/month family plan turns the first sale into an emotional decision. The daily call log turns the renewal into a non-decision. Senior living facilities and home care agencies license the monitoring layer at $10K to $50K per year for fleet-wide deployment. $1M to $10M ARR is in reach with a clean B2C and B2B hybrid motion.

• Why it might fail: Trust is everything in elder care. If the AI feels robotic, families churn within a week. The wedge is hand-delivering the first 20 setups, dialing in tone and call times per family, and proving warmth before scaling. If five questions reliably surface 80% of real concerns, the model works.

workouts this week

at-home

5 rounds for time:

• 20 push-ups

• 30 air squats

• 20 sit-ups

• 15 jump lunges

• 30-second plank

Rest 60 seconds between rounds. Score = total time.

gym

Full body conditioning. 4 rounds, 45 seconds on / 15 seconds rest, of:

• Goblet squat

• Dumbbell push press

• Renegade row

• Kettlebell swing

• Box jumps

Rest 60 seconds between rounds.

Tips:

• Pick a weight you can move with clean form for the full 45 seconds

• Stay tight on the renegade rows. No twisting at the hips.

outdoors

• 1km jog (warm-up)

• 4 rounds: 400m run, 15 push-ups, 15 sit-ups, 10 burpees

• 1km jog (cool-down)

• Finish with 5 minutes of stretching

tweet of the week

this is the one that sparked this week's essay:

— # (#)

my plugs

• Apply for The Trading Post. Deal-by-deal private investment opportunities in Canadian SMEs. Apply here →

• Book your free Exit Audit. We guarantee we'll find hidden profit in your business. Start here →

• Schedule a confidential call to discuss selling your business.

• Download a FREE copy of my Million Dollar Business Exit Guide

• Subscribe to my YouTube Channel

• Subscribe to Main Street Memo for the best tips on buying small businesses.

• Follow me on socials: X + insta + linkedin

every second counts